


Experimentation is Fun

by Izissia



Category: RWBY
Genre: Ass Play, Boyfriends, Breast Growth, Crossdressing, Dildos, F/M, Feminization, Flared Dildos, Hair Brushing, Hair-pulling, Kissing, Lipstick & Lip Gloss, Lube, Makeover, Makeup, Manicures & Pedicures, Neck Kissing, Panties, Rough Kissing, True Love, Vaginal Sex, consensual feminization, horsecock, rimjob
Language: English
Status: Completed
Published: 2019-05-26
Updated: 2019-05-26
Packaged: 2020-03-19 20:09:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 2,886
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18977524
Author URL: https://archiveofourown.org/users/Izissia/pseuds/Izissia
Summary: Jaune and Pyrrha are a dream couple, but unfortunately their sex life could be better. Jaune encourages Pyrrha to imagine her ideal sex partner, and it turns out that's jaune.But a girl.They go on an adventure to try to make Pyrrha's fantasies a reality.Jaune's into it, it's cool.





	1. Chapter 1

"Ah.. Ah.. Oh Jaune.." Pyrrha forced out some fake moans as the bed rocked beneath them faintly. She lifts her ass higher, angling her hips down, desperate to feel something more. "Jaune.." The boredom on her voice was impossible to hide. "Jaune." she wasn't moaning now, she gave the thrusting boy a look. "I don't think, this is working?" the invincible girl pouts out softly as she begins to pull away her hips from that pale white cock.  
"I know Pyrrha. I tried to do it more like you asked but..." Pwap! His stiffy was tugged free from Pyrrha's walls. "It feels really good for me?" he gave her a hopeful look, as though that would cheer her up.  
It didn't.

"I don't know what it is Jaune.." Pyrrha turns to face the boy, Pressing her bare chest to his own as she cupped his cheek sweetly. Her lips lingered dangerously close to his own, sadness in her eyes before she leans forwards and gives him a gentle kiss.  
"I love you Pyrrha." Jaune pants out, pulling his lower lip free from each of the Nikos's.  
"I love you too but.. Maybe you're just, not my type?" Pyrrha felt awful to say it, but she couldn't deny her bodies... Total lack of desire. She truly was in love with this boy, and the sweet kiss she'd just been given had her nipples stiffening against his bare chest. But when it came to.. Sex. It was absolutely worthless.  
She'd endured it for a while, and Jaune always put the sincerest of efforts in. Listening to her every suggestion with heartfelt sincerity. But the spark never caught, no matter how hopeful Pyrrha was. And she'd had enough of Jaune cumming, and her just having to feel good for him.

"P-Pyrrha." Jaune's voice cracked slightly. "Close your eyes and.. And imagine your dream partner." Jaune pushes himself forwards, grinding his chest against hers, grinding his crotch into her own.  
"He's you.. Tall, blonde.. But.." Pyrrha's thighs pushed inwards, her eyes falling shut.  
"B honest, Pyrrha." Jaune let out a soft moan, his warm breath trailing along the redhead's nape. He loops his arms around her lower back, palms flat on the small of her back, holding her naked body in a loving embrace. His figure to her own.  
"He has longer hair and.. He's less handsome.." Pyrrha trembled, letting herself get laid down onto her back. "It's you but just... Uhmm..." Pyrrha didn't know how to say it, didn't know how to phrase it. How COULD she say something like this to her boyfriend.  
"Just imagine them, okay?" Jaune let out an ever so soft whisper, pushing his crotch along Pyrrha's own. His pale cock flopped along her crotch, dragging the underside along her hairless cuntlips.  
"J-Jaune.. It is you. Okay? I'm not imagining anyone e-" Pyrrha began to babble, her eyes peeking open to look up at the blonde boy.  
"I know." the blonde kisses her weakly again, a sweet little smooch. He pumps forwards softly. Pyrrha's eyes shut again as she writhes her hips up along the boys own. Dragging her soft, wet mons along that shaft. She leans on her back, running her fingers through Jaune's hair.  
"Longer.." She whispers as they spill free from his soft golden locks. "S-Stop cutting your hair, grow it out for me.." Pyrrha whimpers, a needy begging sound rolling from her lips.  
Jaune was dry humping her, dragging his crotch into her bare naked frame. He gave weak, drawn out thrusts. Smearing his lap into her own. Pyrrha, with her eyes still closed ran her hands along Jaune's features, from his hair to his cheeks, down to his chest.  
She rests her palms on each of his nipples and lets out a strained confession. "B-Bigger..." She squeaks. But her pussy clamps and twitches. Tugging on Jaune's flat, defined chest. She grew more excited as she fantasized.  
"I don't know if I can-" Jaune starts. Pyrrha cuts him off.  
Whispering out a "Shhh..." As her hairless slit trembled. She slides her hands from the boys chest towards his waist. One hand reaches down, pushing between his asscheeks. The other cradles his balls. "Shave these.. Completely. P-Please.." Pyrrha was so enraptured with her vivid fantasy, Jaune's soft blonde pubes spill through her digits."I uhmm.. Guess." Jaune would agree to anything, Pyrrha looked like she was really, truly enjoying herself. He let the girl take control, only matching her thrusts and pushes, grinding down into her. Jilling his crotch into her body.  
"Of course. Of course." he whispers, mostly to himself as Pyrrha let out a soft, drawn out moan.  
"Just like that. Oh Jaune, you look so good.." Pyrrha's fingers prodded against Jaune's asscheeks, probing between his curves.  
"E-Easy P.. I'm not used to.. Oh~" he lets out a breathless moan as those two fingers probe along his rimhole, wriggling her fingertips into his pucker. Pyrrha lets out yet another moan, grinding into Jaune's rock hard shaft like it was a dildo dragging along her cunt. She took control, and pounds her fingers into the boys rim.  
"Jaune.. Jaune.." Pyrrha was laying on her back, legs lifted, chest pushed up some so she could grope at Jaune's ass. She held her eyes tight shut as she fantasized about the most beautiful blonde girl the school had ever seen. She rams two fingers tight into Jaune's ass and let out a trembling gasp as she bucks harshly against that dick, forcing it to drag along her most private spots, teasing her clitty again and again.  
"Oh.. Jaune~!" the sight of Pyrrha moaning for him for the first time in forever drove Jaune wild, the two fingers in his ass pushed him to gush his steamy, white ropes of cum across her stomach as Pyrrha trashed and ground in a wholly selfish way, getting herself off with the blonde boy.  
Her clear gush streaks along Jaune's lap, soaking him through with her wetness as she let out an eager moan. Cumming for the first time with the help of her lover.

It would take a few days before they did something like that again, Pyrrha glowed with excitement as she spoke of how much fun she'd had with Jaune. Jaune was by all accounts, pretty surprirsed. He didn't know it could make that big of a difference. The pair seemed closer to eachother, and sure enough Jaune agreed to something more dramatic.  
Dress up.


	2. Experimentation is Fun Pt2

**Summary for the Chapter:**

> Jaune tries crossdressing for the first time~

Jaune sat in front of the mirror, Pyrrha running the hairbrush through his growing blonde mane. She lets out a breathless moan, "You look so good, darling." she spoke with warmth and sincerity, "And your hair is so soft." she sweetly cups her lovers cheek and presses an eager, sloppy kiss to his maw.  
"Mhmmmm~" Jaune was conflicted, Pyrrha's affection felt so good but, he couldn't hide his longer hair from the rest of their friends. It was one thing to dress up for sex with her, but she wanted real, permanent changes and he felt anxiety in his stomach struggling to come to terms with them. He breaks the kiss, catching sight of himself in the mirror. Pyrrha smiles as he looks doubtful for a second.   
"Here." the Nikos begins to apply soft pink lipstick to Jaune's plump maw. "Do this for me, and I'll eat your ass, how you like." her voice was dripping with desire as the golden tube liberally smeared the soft, pink wax along Jaune's feminine maw.  
Jaune steps into his pretty, pink panties. The ones with the bow on the front, Pyrrha's favorite. His smooth, clean shaven balls spilled into the constricting fabric. His slender cock looked totally different in them. Pyrrha moans and gives his crotch an eager kiss before straightening herself out and continuing Jaune's makeup.  
The blonde boy slips into the borrowed girls outfit. Nora hadn't asked too many questions, and her proportions were similar enough to Jaune's own that they wouldn't need altering.  
His rock hard stiffy dangles out of the tiny pink panties as the skirt was tugged up over his waist. Pyrrha helps affix his training bra, she gropes his chest through the fabric. "I wish they were bigger." Pyrrha's soft lips suckle on Jaune's ear.

He looks into the mirror again as his bra was tucked beneath the white undershirt, and then the snazzy black coat. Pyrrha was dripping with lust. She shoves Jaune over, bending him across the side of their bed and hikes up that skirt. "Fatter~" she breathes to herself. Jaune had been so accommodating, and in return, Pyrrha had gotten greedier and greedier.  
She hikes that skirt up. "P-Pyrrha.." Jaune moans, his dick twitching beneath his skirt. Even if he struggled to recognize the person in the mirror, he had to admit, this felt pretty good. Especially seeing his girlfriend like that.   
Pyrrha yanks those panties down and uncorks a small bottle, the shiny, shimmering lubricant was dumped messily all over Jaune's rear. Leaving his backside glistening, dripping with oil. "Jaune you make such a good girl." Pyrrha moans, pressing her face into his perky ass and pressing an eager kiss to the boys rimhole.  
"I don't know if I'm..." Jaune started, before the warm wet muscle darts into his rim and he let out a low, drawn out moan. "F-For you, Pyrrha." he breathes, lurching forwards his tongue spills from his lips as he grips the bedsheets with both hands.  
Pyrrha's fingers curl into Jaune's asscheeks, spreading them apart as her lips latch against that asshole. Her tongue darts forwards immediately, that lubed up pucker effortlessly taking down her slimy wet appendage. She tonguefucks that rear with a hunger, her features tilting downwards and pressing her nostrils to that rim. Before dragging her face down, down. Her lips pop free from that ass, and she presses a loving kiss to Jaune's taint instead. "Like this, Jaune.." She grabs at the boy's rock hard cock and angles it down, pushing the pretty pink panties down lower to manhandle that rigid, pale pillar. She squeezes the boys thighs, parting them, and then squishing them tight around that dick. Jaune grunts and moans as his dick was devoured by his pale white thighflesh. Pinned between them.

Pyrrha leans back and salivates at the perfectly smooth, perfectly effeminate rear before her. Dick devoured by his curves. She gropes those asscheeks and rams her face into that ass again. Shlrp~ Her tongue assaults that rim, spiraling against its contours and lunging into that ass. She gropes those bootycheeks, her tongue darts forwards, plunging deep into that rear.   
Jaune's eyes light up and he lifts his hips up behind him, thrusting his ass back onto the skilled tongue of his girlfriend. "Mhmmm.. Jaune, keep it squeezed like that. Even when you cum, understand?" even as she spoke she lashed her tongue along that rim.  
"Yes.. Pyrrha..." The fat assed boy pushes his rear back onto tha tongue and submits to the intense tonguing. His tight pucker squeezes around that tongue, his dick twitches wildly as he clamps his thighs firmly around it. His cock was desperate to lift, but he held it down and.. "Pyrrha~!" he cries as his steamy white ropes of cum poured into his plush thighs. The streaks and ropes tried to gush and spray everywhere, but they were poured straight into the fleshy white prison of his thighs. "Pyrrha can I.."  
"Try to last as long as you can." it was impossible, every time his dick convulsed it demanded tospring straight up and spray with triumph. Jaune held his cock down for as long as he could before his pantyclad prick bounces upright and streaks the last few ropes of cum all over the bed.  
"Does your ass feel good, Jaune?" Pyrrha moans out softly, pulling her face free from that glistening wet asscrack.  
"So good, it always does with you." he breathes as his dick falls flopy, his balls tensed and drained into his panties.  
"Good." Pyrrha runs her fingers along the boys abs, peppering his back in kisses.  
"I have an idea, for next time~" Pyrrha swoons.


	3. Experimentation is Fun Pt3

**Summary for the Chapter:**

> Aaand the final chapter for now.
> 
> Jaune gets a dildo up his buttt.

Date night. Jaune applies the soft pink sheen to his lips, his makeup immaculate, he'd gotten good at it. He could pass for his own sister as he smacks his lips together. His long blonde hair spills down his back. His friends had been so delightful and supportive, and of course. Pyrrha had been too.  
"Hey, babe." she kisses his cheek, and then his lips. Her hands roam along his sides, running over his tits. Thanks to the help of some aura, Jaune had some pretty cute, perky tits. Easily enough to fill out his training bra. Her fingers continue drifting down to his skirt as her tongue overpowers his own effortlessly. She was in charge, and she loved it. Jaune kinda loved it too. Moaning in pleasure as he let Pyrrha make him so pretty, make him into something she desired above all other. Pyrrha lifts up his skirt and breaks the kiss to let out a delighted moan at the sight of that rock hard cock jutting out of his panties. "You look so~oo good." Pyrrha drools. Tugging free a duo of large, flared dildos.  
Jaune's high heels click along the floor as he primes himself over that toy. Squatting his ass down, "Do you wanna do the honors?" his softer voice chimes for Pyrrha. Who of course, eagerly gropes and kneads his ass. Kissing at his pucker before she drools another bottle of oily lube alll over that bubblebutt. He grinds his hips back gracefully onto his loving girlfriends touch. Sitting his trained ass against the ebony flare beneath him.  
Pyrrha lubes her own ass up and smiles at her boyfriend. Her own juicy rear stuffs down onto her matching extra large toy. She groans in pleasure, grabbing at one of Jaune's hands. The girlyboy's dick had a ribbon tied around the base, and it was rock fucking hard. Bouncing with every pump as the salacious pair bounced their asses on their veiny, fat toys!  
Pyrrha lurches forwards, her manicured nails dig into Jaune's long blonde hair and she tonguefucks the boy deeply. "Jaune~" she moans between kisses, hungrily tonguefucking her lover. "Would you ever let.. A real cock go in there?" she arcs her back, still holding onto one of Jaune's hands as their steamy, sweaty sin grew more and more excited.  
"I don't... Know." Jaune gnawed on his lip, Pyrrha drags her tongue along his neckline. "If it'd make you happy then..~"  
"Oh my god, yes Jaune!" Pyrrha throws her head backwards and drags her hand along her crotch. Skilfully playing with her cuntlips as her tight pucker swallows the horsecock toy in her ass down to the root. She moans and writhes, still holding hands with Jaune. "How long are you going to.. Hah.. Last?~" she gave the boy a lust filled look.  
"N-Not long with you looking like that!" Jaune grits his teeth, his head spinning, pounded with desire.  
"Let's cum together!" whap, shlap. Their slick wet asses thump against the bases of their toys as Jaune gushes hot white ropes of cum all towards his busty redhead girlfriend. Pyrrha grabs him again and locks lips with him passionately, lovingly. She sucks his tongue down as they cum in unison.

Pyrrha pushes forwards, Jaune slides onto his back as his redhead girlfriend straddles him. "I could really get used to this." she moans, sitting her ass down atop his spent cock. She strokes his cheek sweetly and kisses his lips deeply.  
Jaune had gotten used to his long blonde hair and his widened hips. He'd gotten used to stuffing his training bra and to how excited Pyrrha had gotten when she saw his panties. Right now he was laying in his bed, with Pyrrha cuddled up to him, makeup slightly messy, outfit long discarded. She slowly wraps her thighs around his cock as she leans back into his arms.  
"Jaune, are you a girl?~" Pyrrha pants as she looks up at the boy.  
"With you.. For you? Yeah, I think I am." he softly squeezes her tits as he grinds his chest into her back. "But out there?" he muses in thought as he looks her in the eyes. "I dunno. I don't think so." he pushes himself forwards, rolling Pyrrha onto her front, bucking down into her thighs from behind. "It's complicated, I guess? I don't wanna be June or Summer or anything, I still wanna be Jaune." he pushes down eagerly, Pyrrha lets out a soft moan as her thighs were fucked.  
She wriggles in his grasp, trying to kiss back at him.  
"Just.. Jaune who wears skirts?" Pyrrha breathes, looping her arm around his neckline.  
"Yeah." he tilts his head forwards and kisses her prone bone cheek.  
"Aim for my ass, baby~" Pyrrha shifts beneath him, tugging her arm away from his neck, she spreads her asscheeks apart.  
Jaune nods, a few firm pumps later and he's gushing cum across her spread apart asscheeks. "I love you~" he moans in delight.  
"I love you too, Jaune." she rolls onto her back. Squish, her bootycheeks squelch into the bed. Her thighs spread apart and she pulls Jaune atop her, cuddling up for the night.

**Notes for the Chapter:**

> Wow it's my cool discord again~
> 
> https://discord.gg/2yq2zUP
> 
> Also follow me on twitter~
> 
> https://twitter.com/IzissiaD

**Author's Note:**

> Wow I've got a cool discord.  
> https://discord.gg/2yq2zUP
> 
> Wow follow me on twitter.  
> https://twitter.com/IzissiaD


End file.
